WO2006130403A1 - Derives heteroaryle phenylalkyle substitues - Google Patents

Derives heteroaryle phenylalkyle substitues Download PDF

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WO2006130403A1
WO2006130403A1 PCT/US2006/020049 US2006020049W WO2006130403A1 WO 2006130403 A1 WO2006130403 A1 WO 2006130403A1 US 2006020049 W US2006020049 W US 2006020049W WO 2006130403 A1 WO2006130403 A1 WO 2006130403A1
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alkyl
halo
formula
hydrogen
alkoxy
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PCT/US2006/020049
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English (en)
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John W. Lyga
Frank Zawacki
Larry Y. Zhang
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Bayer Cropscience Ag
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Priority to AU2006252768A priority Critical patent/AU2006252768A1/en
Priority to MX2007015002A priority patent/MX2007015002A/es
Priority to US11/915,974 priority patent/US8017635B2/en
Priority to JP2008514694A priority patent/JP2008545744A/ja
Priority to BRPI0613535-8A priority patent/BRPI0613535A2/pt
Priority to EP06760332A priority patent/EP1890694A4/fr
Publication of WO2006130403A1 publication Critical patent/WO2006130403A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to novel compounds and their use in controlling insects and acarids.
  • it pertains to phenylalkyl substituted heteroaryl derivatives and agriculturally acceptable salts thereof, compositions containing them and methods for their use in controlling insects and acarids.
  • insects in general can cause significant damage, not only to crops grown in agriculture, but also, for example, to structures and turf where the damage is caused by soil-borne insects, such as termites and white grubs. Such damage may result in the loss of millions of dollars of value associated with a given crop, turf or structures.
  • Insecticides and acaricides are useful for controlling insects and acarids which may otherwise cause significant damage to crops such as wheat, corn, soybeans, potatoes, and cotton to name a few.
  • insecticides and acaricides are desired which can control the insects and acarids without damaging the crops, and which have no deleterious effects to mammals and other living organisms.
  • novel phenylalkyl substituted heteroaryl derivatives are surprisingly active in the control of insects and acarids when used in the insecticidal and acaricidal compositions and methods of this invention.
  • the novel derivatives are represented by the following general formula I:
  • R and R 3 are independently selected from hydrogen, halogen, hydroxy, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 5 )alkenyl, (C 2 -C 5 )alkynyl, halo(C 1 -C 3 )alkyl, (C 1 - C 3 )alkoxy, halo(C 1 -C 3 )alkoxy, (C 1 -C 3 )alkylthio, halo(C 1 -C 3 )alkylthio, (C 1 - C 3 )alkylsulfonyl, halo(C 1 -C 3 )alkylsulfonyl, cyano, nitro, amino; optionally substituted amino wherein the optional substituent is selected from (C 1 -C 4 )alkyl, (C 1 -C 3 )alkylcarbonyl and (C 1 -C 3 )
  • K is selected from O, S, NR 19 , and NOR 19 , where R 19 is hydrogen, (C 1 -C 4 )alkyl, halo(C 1 -C 4 )alkyl, aryl and aryl(C 1 -C 4 )alkyl;
  • L is selected from hydrogen, (C 1 -C 3 )alkyl, halo(C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy, (C 1 -
  • M is selected from O, S, and NR 19 , where R 19 is as previously described;
  • R 17 and R 18 are independently selected from hydrogen, (C 1 -C 4 )alkyl and halo(C 1 - C 4 )alkyl, or R 17 and R 18 are taken together with -Q(CHR 19 ) e -, where e is an integer of 2 to 4; Q is selected from O, S, and NR 19 , where R 19 is as previously described; R 1 and R 2 are independently selected from hydrogen, halogen and (C 1 -C 3 )alkyl;
  • A is selected from O, S, OCH 2 and (CH 2 ) f where the asterisk denotes attachment to B, and f is an integer selected from 1, 2 and 3;
  • B is selected from CH 2 , O, S and NR where R is selected from hydrogen, (C 1 -
  • C 3 )alkyl (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy(C 1 -C 3 )alkyl, aryl(C 1 -C 3 )alkyl, (C 1 -C 4 )alkenyl(C 1 - C 3 )alkyl, halo(C 2 -C 4 )alkenyl(C 1 -C 3 )alkyl, di(C 1 -C 3 )alkylphosphonate, (C 1 -
  • R 20 is as previously described, and g is an integer selected from 0, 1 or 2; b is an integer selected from 0, 1, 2, 3, or 4; and when b is 1 or more,
  • R 7 and R 8 are independently selected from hydrogen, halogen, (C 1 -C 4 )alkyl, cyclo(C 3 -C 6 )alkyl, halo(C 1 -C 4 )alkyl, or aryl; E is selected from
  • c is an integer selected from 0, 1, 2, 3 or 4; and when c is 1 or more, R 9 and R 10 are independently selected from hydrogen, (C 1 -C 4 )alkyl, haIo(C 1 -
  • R 11 is selected from (C 1 -C 6 )alkyl, tri(C 1 -C 6 )alkylsilyl,
  • R 21 through R 25 are independently selected from hydrogen, halogen, (C 1 - C 6 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 - C 6 )alkyl, cyclo(C 3 -C 6 )alkyl, halo(C 2 -C 4 )alkenyl, halo(C 2 -C 4 )alkynyl, (C 1 - C 6 )alkoxy, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )alkynyloxy, halo(C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkenyloxy, halo(C 2 -C 4 )
  • C 6 )alkoxycarbonyl or R c and R d are taken together to form a 5- or 6-membered saturated or unsaturated ring containing carbon, O, N, or S; (C 1 - C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarbonyloxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 - C 6 )alkoxycarbonyloxy, (C 1 -C 6 )alkylaminocarbonyl, (C 1 - C 6 )alkylaminocarbonyloxy, tri(C 1 -C 6 )alkylsilyl, di(C 1 -C 6 )alkylphosphinoyl, aryl, aryloxy, and aryl(C 1 -C 6 )alkoxy; and agriculturally-acceptable salts thereof.
  • the present invention also includes compositions containing an insecticidally effective amount of at least one compound of formula I, and optionally, an effective amount of at least one additional compound, with at least one insecticidally compatible carrier.
  • the present invention also includes methods of controlling insects, in an area where control is desired, which comprise applying an insecticidally effective amount of the above composition to the locus of crops, or other areas where insects are present or are expected to be present.
  • the present invention also includes novel intermediates finding utility in the syntheses of compounds of formula I. DETAILED DESCRIPTION OF THE INVENTION
  • the present invention relates to certain new and useful insecticidal and acaricidal compounds, namely phenylalkyl substituted heteroaryl derivatives (hereinafter termed "compounds of formula I") as depicted in general formula I:
  • R and R 3 are independently selected from hydrogen, halogen, hydroxy, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 5 )alkenyl, (C 2 -C 5 )alkynyl, halo(C 1 -C 3 )alkyl, (C 1 - C 3 )alkoxy, halo(C 1 -C 3 )alkoxy, (C 1 -C 3 )alkylthio, halo(C 1 -C 3 )alkylthio, (C 1 - C 3 )alkylsulfonyl, halo(C 1 -C 3 )alkylsulfonyl, cyano, nitro, amino; optionally substituted amino wherein the optional substituent is selected from (C 1 -C 4 )alkyl,
  • (C 1 -C 3 )alkylcarbonyl and (C 1 -C 3 )alkoxycarbonyl; optionally substituted imidazolyl, optionally substituted imidazolinyl, optionally substituted oxazolinyl, optionally substituted oxazolyl, optionally substituted oxadiazolyl, optionally substituted thiazolyl, optionally substituted pyrazolyl, optionally substituted triazolyl, optionally substituted furanyl, optionally substituted tetrahydrofuranyl, optionally substituted dioxolanyl, optionally substituted dioxanyl, -C( K)-L, and -C(R 17 )-M-R 18 , wherein the optional substituent is selected from (C 1 -C 4 )alkyl, halogen, halo(C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 - C 4 )alk
  • K is selected from O, S, NR 19 , and NOR 19 , where R 19 is hydrogen, (C 1 -C 4 )alkyl, halo(C 1 -C 4 )alkyl, aryl and aryl(C 1 -C 4 )alkyl; L is selected from hydrogen, (C 1 -C 3 )alkyl, haIo(C 1 -C 3 )EIlCyI, (C 1 -C 3 )EIkOXy, (C 1 -
  • M is selected from O, S, and NR 19 , where R 19 is as previously described;
  • R 17 and R 18 are independently selected from hydrogen, (C 1 -C 4 )alkyl and haIo(C 1 - C 4 )alkyl, or R 17 and R 18 are taken together with -Q(CHR 19 ) e -, where e is an integer of 2 to 4;
  • Q is selected from O, S, and NR 19 , where R 19 is as previously described;
  • R 1 and R 2 are independently selected from hydrogen, halogen and (C 1 -C 3 )alkyl;
  • A is selected from O, S, * OCH 2 and (CH 2 ) f where the asterisk denotes attachment to B, and f is an integer selected from 1 , 2 and 3 ;
  • B is selected from CH 2 , O, S and NR 20 where R 20 is selected from hydrogen, (C 1 -
  • C 3 alkylcarbonyl, halo(C 1 -C 3 )alkylcarbonyl, (C 1 -C 3 )alkoxy(C 1 -C 3 )alkylcarbonyl, arylcarbonyl and (C 1 -C 3 )alkylsulfonyl; provided that A and B are not simultaneously O or S; R 4 is hydrogen;
  • R 5 and R 6 are independently selected from halogen; a is an integer selected from 0 or 1 ; and when a is 1 ,
  • R 20 is as previously described, and g is an integer selected from 0, 1 or 2; b is an integer selected from 0, 1, 2, 3, or 4; and when b is 1 or more,
  • R 7 and R 8 are independently selected from hydrogen, halogen, (C 1 -C 4 )alkyl, cyclo(C 3 -C 6 )alkyl, halo(C 1 -C 4 )alkyl, or aryl; E is selected from
  • c is an integer selected from 0, 1, 2, 3 or 4; and when c is 1 or more, R 9 and R 10 are independently selected from hydrogen, (C 1 -C 4 )alkyl, haIo(C 1 -
  • R 11 is selected from (C 1 -C 6 )alkyl, tri(C 1 -C 6 )alkylsilyl,
  • R 21 through R 25 are independently selected from hydrogen, halogen, (C 1 - C 6 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, halo(C 1 -C 6 )alkyl, hydroxy(C 1 - C 6 )alkyl, cyclo(C 3 -C 6 )alkyl, halo(C 2 -C 4 )alkenyl, halo(C 2 -C 4 )alkynyl, (C 1 - C 6 )alkoxy, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )alkynyloxy, halo(C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkenyloxy, halo(C 2 -C 4 )
  • Preferred phenylalkyl substituted azole derivatives from the group set forth above are those where:
  • R and R 3 are independently selected from halogen and (C 1 -C 3 )alkyl; R 1 , R 2 and R 4 are hydrogen;
  • R 5 and R 6 are halogen
  • A is (CH 2 ) f where f is 1 ;
  • B is O; a is an integer selected from 0 or 1, and when a is 1, D is selected from O, CH 2 and OCH 2 ; b is an integer selected from 0, 1, 2, 3 or 4, and when b is 1 or more, R 7 and R 8 are each hydrogen;
  • E is formula (E1), formula (E4), formula (71),or formula (E8); c is an integer selected from 0, 1, 2, 3 and 4, and when c is 1 or more, R 9 and R 10 are each hydrogen; d is 0 or 1 ; and when d is 1, G is selected from O or S; and
  • R 11 is selected from formula (R 11 -1), formula (R 11 -2), formula (R 11 -3), or formula
  • phenylalkyl substituted heteroaryl derivatives of the group set forth above are those where:
  • R and R 3 are each chlorine; a is 1 and D is O; b is an integer selected from 2, 3 or 4;
  • E is formula (E1) or formula (E7); c is an integer selected from 0 or 1 ; d is 0; and
  • R 11 is (R 11 -1) or (R 11 -2).
  • the compounds of the present invention may possess asymmetric centers, which can give rise to optical enantiomorphs and diastereomers.
  • the compounds may exist in two or more forms, i.e., polymorphs, which are significantly different in physical and chemical properties.
  • the compounds of the present invention may also exist as tautomers, in which migration of a hydrogen atom within the molecule results in two or more structures, which are in equilibrium.
  • the compounds of the present invention may also possess acidic or basic moieties, which may allow for the formation of agriculturally acceptable salts or agriculturally acceptable metal complexes.
  • Agriculturally acceptable salts and metal complexes include, without limitation, for example, ammonium salts, the salts of organic and inorganic acids, such as hydrochloric acid, sulfonic acid, ethanesulfonic acid, trifluoroacetic acid, methylbenzenesulfonic acid, phosphoric acid, gluconic acid, pamoic acid, and other acid salts, and the alkali metal and alkaline earth metal complexes with, for example, sodium, potassium, lithium, magnesium, calcium, and other metals.
  • the methods of the present invention comprise causing an insecticidally effective amount of a compound of formula I to be administered to insects in order to kill or control the insects.
  • Preferred insecticidally effective amounts are those that are sufficient to kill the insect. It is within the scope of the present invention to cause a compound of formula I to be present within insects by contacting the insects with a derivative of that compound, which derivative is converted within the insect to a compound of formula I. This invention includes the use of such compounds, which are referred to as pro-insecticides.
  • compositions containing an insecticidally effective amount of at least one compound of formula I relates to compositions containing an insecticidally effective amount of at least one compound of formula I.
  • compositions containing an insecticidally effective amount of at least one compound of formula I, and an effective amount of at least one additional compound are also useful.
  • Another aspect of the present invention relates to methods of controlling insects by applying an insecticidally effective amount of a composition as set forth above to a locus of crops such as, without limitation, cereals, cotton, vegetables, and fruits, or other areas where insects are present or are expected to be present.
  • a locus of crops such as, without limitation, cereals, cotton, vegetables, and fruits, or other areas where insects are present or are expected to be present.
  • the present invention also includes the use of the compounds and compositions set forth herein for control of non-agricultural insect species, for example, dry wood termites and subterranean termites; as well as for use as pharmaceutical agents.
  • the compounds of the present invention are expected to be effective against certain endo- and ectoparasites, such as insects and worms, which prey on animals.
  • animal parasites include, without limitation, Gastrophilus spp., Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis, and other species.
  • alkyl and “alkoxy”, used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
  • haloalkyl and
  • haloalkoxy used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms, wherein one or more hydrogen atoms have been replaced with halogen atoms, for example, trifluoromethyl or 2,2,2- trifluoroethoxy.
  • alkenyl and “alkynyl” used alone or as part of a larger moiety includes straight or branched chains of at least two carbon atoms containing at least one carbon-carbon double bond or triple bond, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
  • aryl refers to an aromatic ring structure, including fused rings, having six to ten carbon atoms, for example, phenyl, indanyl, indenyl, naphthyl or 5,6,7,8-tetrahydronaphthyl.
  • heteroaryl refers to an aromatic ring structure, including fused rings, in which at least one of the atoms is other than carbon, for example, without limitation, sulfur, oxygen, or nitrogen. Heteroaryl rings include, without limitation, for example, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazolyl or thiadiazolyl.
  • DMF refers to N,N- dimethylformamide.
  • THF refers to tetrahydrofuran.
  • TEA refers to triethyl amine.
  • DIEA refers to N,N-diisopropylethylamine.
  • HBTU O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate.
  • HOBT 1-hydroxybenzotriazole hydrate.
  • TFA trifluoroacetic acid.
  • halogen or halo refers to fluorine, bromine, iodine, or chlorine.
  • ambient temperature for example, in reference to a chemical reaction mixture temperature, refers to a temperature in the range of 20 °C to 30 °C.
  • insecticidal or “acaricidal”
  • insecticide or “acaricide” refers to a compound of the present invention, either alone or in admixture with at least one additional compound, or with at least one compatible carrier, which causes the destruction or the inhibition of action of insects or acarids.
  • independently selected from refers to the possibility that moieties, for example R 5 and R 6 , may be the same or they may be different within the group that the selection is made.
  • phenylalkyl substituted heteroaryl derivatives of formula I can be synthesized by methods that are individually known to one skilled in the art from available intermediate compounds.
  • Scheme 1 illustrates a general procedure for synthesizing phenylalkyl substituted heteroaryl derivatives of formula I, inter alia, where, for example, R 1 , R 2 , R 4 R 7 , R 8 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1 , and D is O; b is 2; E is (E1); c and d are 0; R 11 is 4-chlorophenyl:
  • the known compound 2,6-dichloro-4- phenylmethoxyphenol was reacted under basic conditions with, for example a haloalkyl alcohol such as 2-chloroethanol, affording the corresponding alcohol (Al), for example, 2-(2,6-dichloro-4-(phenylmethoxy)phenoxy)ethan-1-ol.
  • Alcohol (Al) was treated it with hydrogen gas under catalytic hydrogenation conditions, providing intermediate (A2).
  • Intermediate (A2) was treated with, for example 3- bromo-l,l,l-trichloropropane, under basic conditions, affording the corresponding intermediate (A3).
  • the azidoethanol intermediate (A4) was reacted with an appropriately substituted ethynylbenzene in the presence of sodium ascorbate and a catalytic amount of copper (II) sulfate pentahydrate, providing compounds of formula I, such as, 5-(3,3-dichloroprop-2-enyloxy)-1,3-dichloro-2-(2-(4-(4- chlorophenyl)1,2,3-triazolyl)ethoxy)benzene.
  • This process is described in detail in Example 1 set forth below.
  • Scheme 2 illustrates a general procedure for synthesizing phenylalkyl substituted heteroaryl derivatives of formula I, inter alia, where, for example, R , R 2 , R 4 R 7 , R 8 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; b is 2; E is (E7); c and d are 0; R 11 is 3- trifluoromethylphenyl :
  • Scheme 3 illustrates a general procedure for synthesizing phenylalkyl substituted heteroaryl derivatives of formula I, inter alia, where, for example, R 1 , R 2 , R 4 R 7 , R 8 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; b is 2; E is (E8); c and d are 0; R 11 is 4- trifluoromethylphenyl :
  • Scheme 4 illustrates a general procedure for synthesizing phenylalkyl substituted heteroaryl derivatives of formula I, inter alia, where, for example, R 1 , R 2 , R 4 R 7 , R 8 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; b is 1; E is (E14); c and d are 0; R 11 is 3- trifluoromethylphenyl:
  • the present insecticidal compounds may be formulated as a granular of relatively large particle size (for example, 8/16 or 4/8 US Mesh), as water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as aqueous emulsions, as solutions, or as any of other known types of agriculturally-useful formulations, depending on the desired mode of application. It is to be understood that the amounts specified in this specification are intended to be approximate only, as if the word "about" were placed in front of the amounts specified.
  • insecticidal compositions may be applied either as water-diluted sprays, or dusts, or granules to the areas in which suppression of insects is desired. These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient.
  • Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns.
  • a typical dust formulation useful herein is one containing 1.0 part or less of the insecticidal compound and 99.0 parts of talc.
  • Wettable powders also useful formulations for insecticides, are in the form of finely divided particles that disperse readily in water or other dispersant.
  • the wettable powder is ultimately applied to the locus where insect control is needed either as a dry dust or as an emulsion in water or other liquid.
  • Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5-80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
  • a useful wettable powder formulation contains 80.0 parts of the insecticidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents. Additional wetting agent and/or oil will frequently be added to a tank mix for to facilitate dispersion on the foliage of the plant.
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated.
  • the percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of active ingredient by weight of the insecticidal composition.
  • Flowable formulations are similar to ECs, except that the active ingredient is suspended in a liquid carrier, generally water.
  • Flowables like ECs, may include a small amount of a surfactant, and will typically contain active ingredients in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition.
  • flowables may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
  • Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long-chain mercaptans and ethylene oxide.
  • Many other types of useful surface-active agents are available in commerce. Surface-active agents, when used, normally comprise 1 to 15% by weight of the composition.
  • compositions include suspensions of the active ingredient in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
  • Still other useful formulations for insecticidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents.
  • Granular formulations, wherein the toxicant is carried on relative coarse particles, are of particular utility for aerial distribution or for penetration of cover crop canopy.
  • Pressurized sprays, typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low- boiling dispersant solvent carrier may also be used.
  • Water-soluble or water- dispersible granules are free flowing, non-dusty, and readily water-soluble or water- miscible.
  • the granular formulations, emulsifiable concentrates, flowable concentrates, aqueous emulsions, solutions, etc. may be diluted with water to give a concentration of active ingredient in the range of say 0.1 % or 0.2% to 1.5% or 2%.
  • the active insecticidal compounds of this invention may be formulated and/or applied with one or more additional compound.
  • Such combinations may provide certain advantages, such as, without limitation, exhibiting synergistic effects for greater control of insect pests, reducing rates of application of insecticide thereby minimizing any impact to the environment and to worker safety, controlling a broader spectrum of insect pests, safening of crop plants to phytotoxicity, and improving tolerance by non-pest species, such as mammals and fish.
  • Additional compounds include, without limitation, other pesticides, plant growth regulators, fertilizers, soil conditioners, or other agricultural chemicals.
  • an effective amount and concentration of the active compound is of course employed; the amount may vary in the range of, e.g. about 0.001 to about 3 kg/ha, preferably about 0.03 to about 1 kg/ha.
  • higher application rates e.g., four times the rates mentioned above may be employed.
  • the herbicides include, without limitation, for example: N- (phosphonomethyl)glycines such as glyphosate; aryloxyalkanoic acids such as 2,4- D, MCPA, and MCPP; ureas such as isoproturon; imidazolinones such as imazapyr, imazamethabenz, imazethapyr, and imazaquin; diphenyl ethers such as acifluorfen, bifenox, and fomasafen; hydroxybenzonitriles such as ioxynil and bromoxynil; sulfonylureas such as chlorimuron, achlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron, and triasulfuron; 2-(4-aryloxymethyl)glycines such as glyphosate; aryloxyalkanoic acids such as 2,4- D, MCPA, and MCPP;
  • the other insecticides include, for example: organophosphate insecticides, such as chlorpyrifos, diazinon, dimethoate, malathion, parathion- methyl, and terbufos; pyrethroid insecticides, such as fenvalerate, deltamethrin, fenpropathrin, cyfiuthrin, flucythrinate, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin , bifenthrin, cypermethrin, permethrin, resolved cyhalothrin, etofenprox, esfenvalerate, tralomehtrin, tefluthrin, cycloprothrin, bet
  • organophosphate insecticides such as chlorpyrifos, diazinon, dimethoate, malathion, parathion- methyl,
  • the fungicides include, for example: benzimidazole fungicides, such as benomyl, carbendazim, thiabendazole, and thiophanate-methyl; 1,2,4- triazole fungicides, such as epoxyconazole, cyproconazole, flusilazole, flutriafol, propiconazole, tebuconazole, triadimefon, and triadimenol; substituted anilide fungicides, such as metalaxyl, oxadixyl, procymidone, and vinclozolin; organophosphorus fungicides, such as fosetyl, iprobenfos, pyrazophos, edifenphos, and tolclofos-methyl; morpholine
  • the active insecticidal compounds of the present invention are used in combination with at least one additional compound, e.g., with other pesticides such as nematicides
  • the nematicides include, for example: carbofuran, carbosulfan, terbufos, aldecarb, ethoprop, fenamphos, oxamyl, isazofos, cadusafos, and other nematicides.
  • the plant growth regulators include, for example: maleic hydrazide, chlormequat, ethephon, gibberellin, mepiquat, thidiazon, inabenfide, triaphenthenol, paclobutrazol, unaconazol, DCPA, prohexadione, trinexapac-ethyl, and other plant growth regulators.
  • Soil conditioners are materials which, when added to the soil, promote a variety of benefits for the efficacious growth of plants. Soil conditioners are used to reduce soil compaction, promote and increase effectiveness of drainage, improve soil permeability, promote optimum plant nutrient content in the soil, and promote better pesticide and fertilizer incorporation.
  • the soil conditioners include organic matter, such as humus, which promotes retention of cation plant nutrients in the soil; mixtures of cation nutrients, such as calcium, magnesium, potash, sodium, and hydrogen complexes; or microorganism compositions which promote conditions in the soil favorable to plant growth.
  • Such microorganism compositions include, for example, bacillus, pseudomonas, azotobacter, azospirillum, rhizobium, and soil-borne cyanobacteria.
  • Fertilizers are plant food supplements, which commonly contain nitrogen, phosphorus, and potassium.
  • the fertilizers include nitrogen fertilizers, such as ammonium sulfate, ammonium nitrate, and bone meal; phosphate fertilizers, such as superphosphate, triple superphosphate, ammonium sulfate, and diammonium sulfate; and potassium fertilizers, such as muriate of potash, potassium sulfate, and potassium nitrate, and other fertilizers.
  • EXAMPLE 1 This example illustrates one protocol for the preparation of 5-(3,3-dichloroprop-2- enyloxy)-1,3-dichloro-2-(2-(4-(4-chlorophenyl)-1,2,3-triazolyl)ethoxy)benzene
  • the filtrate was concentrated under reduced pressure to a residue.
  • the residue was purified with column chromatography on silica gel using 75:25 heptanexthyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 4.6 grams of the subject compound.
  • the NMR spectrum was consistent with the proposed structure.
  • Step D Synthesis of 4-(3,3-dichloroprop-2-enyloxy)-2,6-dichloro-1-(2- azidoethoxy)benzene as an intermediate
  • the reaction mixture was diluted with 25 mL of methylene chloride and was washed first with 25 mL of water followed by 10 mL of a saturated aqueous sodium chloride solution.
  • the organic phase was dried with magnesium sulfate, filtered and the filtrate concentrated under reduced pressure leaving an oil, which solidified upon standing.
  • the solid was dissolved in 10 mL of DMSO to which 0.32 gram (0.005 mole) of sodium azide was added.
  • the reaction mixture stirred at ambient temperature for about 18 hours at which time the reaction mixture was heated at 60° C for one hour.
  • the mixture was allowed to cool to ambient temperature, diluted with 25 mL of water and extracted with two 25 mL portions of ethyl acetate.
  • Step E Synthesis of 5-(3 ,3 -dichloroprop-2-enyloxy)- 1 ,3 -dichloro-2-(2-(4-(4- chlorophenyl)1,2,3-triazolyl))ethoxy)benzene (Compound 2)
  • To a stirred mixture of 0.36 gram (0.001 mole) of 4-(3,3-dichloroprop-2-enyloxy)- 2,6-dichloro-1-(2-azidoethoxy)benzene and 0.14 gram (0.0001 mole) of l-chloro-4- ethynylbenzene in 5 mL of a 1 to 1 mixture of t-butanol and water was added 0.1 mL of a IM solution of sodium ascorbate in water and a catalytic amount (approximately 0.0002 gram) of copper (II) sulfate pentahydrate.
  • the reaction mixture was allowed to stir at ambient temperature for about 18 hours, and then was diluted with 10 mL of water.
  • the mixture was extracted with two 5 mL portions of ethyl acetate and the combined extracts were dried with magnesium sulfate and filtered.
  • the filtrate was concentrated under reduced pressure providing 0.45 gram of the subject compound as an oil.
  • the NMR spectrum was consistent with the proposed structure.
  • Diisopropyl azodicarboxalate (0.056 gram, 0.00028 mole) was added to a stirred, cold (0 °C) mixture of 0.072 gram (0.00028 mole) of triphenylphosphine, 0.045 gram (0.00021 mole) of 5-(3-trifluoromethylphenyl)-2H-1,2,3,4-tetrazole and 0.075 gram (0.00023 mole) of2-(4-(3,3-dichloroprop-2-enyloxy)-2,6- dichlorophenoxy)ethan-1-ol.
  • the cold reaction mixture stirred for one hour at which time the mixture was concentrated under reduced pressure to a residue.
  • EXAMPLE 3 This example illustrates one protocol for the preparation of 5-(3,3-dichloroprop-2- enyloxy)-1,3-dichloro-2-(2-(3-(4-trifluoromethylphenyl)(1,2,4- triazolyl))ethoxy)benzene (Compound 8-2) Step A Synthesis of 2(-3 ,3 -dichloroprop-2-enyloxy)-2,6- dichlorophenoxy)ethyl methylsulfonate as an intermediate To a stirred mixture of 0.25 gram (0.00075 mole) of 2-(4-(3,3-dichloroprop-2- enyloxy)-2,6-dichlorophenoxy)ethan-1-ol and 0.113 gram (0.00113 mole) of triethylamine in 3.75 mL of THF was added 0.086 gram (0.00075 mole) of methane sulfonyl chloride.
  • reaction mixture was stirred at ambient temperature for one hour. After this time the reaction mixture was diluted with 5 mL of aqueous ammonium chloride solution then extracted with two 7 mL portions of diethyl ether. The extracts were combined, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 0.31 gram of the subject compound as an oil.
  • the reaction mixture was allowed to cool, diluted with 5 mL of aqueous sodium bicarbonate then extracted with 15 mL of a mixture of hexanes and ethyl acetate (7:3).
  • the extract was washed with two 5 mL portions of water and one 5 mL portion of saturated aqueous sodium chloride solution, dried with sodium sulfate and filtered.
  • the filtrate was concentrated under reduced pressure to an oil residue.
  • the oil residue was purified by column chromatography on silica gel, eluted with mixtures of methylene chloride and diethyl ether. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.1 gram of the subject compound as an off-white solid.
  • the crude oil was purified with column chromatography on silica gel using a mixture of hexanes and ethyl acetate (93:7) as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.7 gram of the subject compound.
  • Step B Synthesis of 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy) acetic acid as an intermediate
  • Trifluoroacetic acid (3.0 mL, 0.04 mole) was added and the reaction mixture was allowed to warm to ambient temperature where it stirred for two hours.
  • the reaction mixture was concentrated under reduced pressure leaving a residue.
  • the residue was dissolved in methylene chloride and the solution concentrated under reduced pressure and the resulting residue was dissolved in methylene chloride again.
  • the solution was concentrated under reduced pressure to yield a quantitative amount of the subject compound as a white powder.
  • Step C Synthesis of 5-(3,3-dichloroprop-2-enyloxy)-1,3-dichloro-2((3-(3- trifluoromethylphenyl)(1,2,4-oxadiazol-5-yl))methoxy)benzene (Compound 14-54)
  • reaction mixture stirred for 10 minutes at which time 0.075 gram (0.00037 mole) of 3-(trifluoromethyl)benzamidoxime was added. Upon completion of addition the reaction mixture was stirred at ambient temperature then heated to 112 °C where it stirred for four hours. After this time the reaction mixture was cooled to ambient temperature, diluted with water and extracted with a mixture of hexanes and ethyl acetate (70:30). The extract was washed in succession with two 5 mL portions of water, one 5 mL portion of an aqueous hydrochloric acid solution and one 5 mL portion of aqueous sodium bicarbonate, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue.
  • compounds like the compounds of formula I of the present invention can contain optically active and racemic forms. It is also well known in the art that compounds like the compounds of formula I may contain stereoisomeric forms, tautomeric forms and/or exhibit polymorphism. It is to be understood that the present invention encompasses any racemic, optically active, polymorphic, tautomeric, or stereoisomeric form, or mixtures thereof. It should be noted that it is well known in the art how to prepare optically active forms, for example by resolution of a racemic mixture, or by synthesis from optically active intermediates.
  • R 1 , R 2 , R 4 R 7 , R 8 , R 9 , R 10 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; E is (E1); G is O; providing the following compounds:
  • R 1 , R 2 , R 4 R 7 , R 8 , R 9 , R 10 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; E is (E2); G is O; providing the following compounds:
  • R 1 , R 2 , R 4 R 7 , R 8 , R 9 , R 10 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; E is (E4); G is O; providing the following compounds:
  • R 1 , R 2 , R 4 R 7 , R 8 , R 9 , R 10 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; E is (E7); G is O; providing the following compounds:
  • R 1 , R 2 , R 4 R 7 , R 8 , R 9 , R 10 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; E is (E8); G is O; providing the following compounds:
  • R 1 , R 2 , R 4 R 7 , R 8 , R 9 , R 10 are hydrogen; R, R 3 , R 5 and R 6 are chlorine; A is (CH 2 ) f where f is 1; B is O, a is 1, and D is O; E is (E14); G is O; providing the following compounds:
  • test compounds of formula I are identified by numbers that correspond to those in Table 1 :
  • test compounds of formula I are identified by numbers that correspond to those in Table 1 :
  • Candidate insecticides were evaluated for activity against the tobacco budworm (Heliothis virescens [Fabricius]) in a surface-treated diet test.
  • Heliothis virescens [Fabricius] a surface-treated diet test.
  • one mL of molten (65-70°C) wheat germ-based artificial diet was pipetted into each well of a four by six (24 well) multi-well plate (ID# 430345-15.5 mm diameter x 17.6 mm deep; Corning Costar Corp., One Alewife Center, Cambridge, MA 02140).
  • the diet was allowed to cool to ambient temperature before treatment with the candidate insecticide.
  • solutions of the candidate insecticides were prepared for testing using a Packard 204DT Multiprobe Robotic
  • test was established as described above using sub- multiples of the standard 50 millimolar DMSO solution of candidate insecticide.
  • the standard 50 millimolar solution was diluted by the robot with
  • DMSO dilute solutions of the candidate insecticide.
  • each rate of application placed on the surface of the diet in the 24 multi-well plate, for a total of four rates of application of candidate insecticide in each plate.
  • a second instar tobacco budworm larvae weighing approximately five milligrams. After the larvae were placed in each well, the plate was sealed with clear polyfilm adhesive tape. The tape over each well was perforated to ensure an adequate air supply. The plates were then held in a growth chamber at 25 °C and 60% relative humidity for five days (light 14 hours/day).
  • insecticidal activity for each rate of application of candidate insecticide was assessed as percent inhibition of insect weight relative to the weight of insects from untreated controls, and percent mortality when compared to the total number of insects infested.
  • Insecticidal activity data at selected rates of application from this test are provided in Table 3.
  • the test compounds of formula I are identified by numbers that correspond to those in Table 1.

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Abstract

Certains nouveaux dérivés d'azole substitués phénylalkyle possèdent une activité insecticide inattendue. Ces composés sont représentés par la formule I dans laquelle A, B, D, E, G, a, b, c, d, et R à R11, inclus, sont tels que décrits dans les spécifications. Cette invention concerne aussi des compositions comprenant une quantité efficace insecticide d'au moins un composé représenté par la formule I, et éventuellement une quantité efficace d'au moins un second composé avec au moins un porteur insecticide compatible, ainsi que des techniques de lutte contre les insectes consistant à appliquer ces compositions sur un site où ces insectes sont présents ou sont supposés être présents.
PCT/US2006/020049 2005-06-02 2006-05-24 Derives heteroaryle phenylalkyle substitues WO2006130403A1 (fr)

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MX2007015002A MX2007015002A (es) 2005-06-02 2006-05-24 Derivados de heteroarilo sustituidos con fenilalquilo.
US11/915,974 US8017635B2 (en) 2005-06-02 2006-05-24 Phenylalkyl substituted heteroaryl derivatives
JP2008514694A JP2008545744A (ja) 2005-06-02 2006-05-24 フェニルアルキル置換ヘテロアリール誘導体
BRPI0613535-8A BRPI0613535A2 (pt) 2005-06-02 2006-05-24 derivados de heteroarila substituìda por fenilalquila
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MX2007015002A (es) 2008-02-15
AU2006252768A1 (en) 2006-12-07
CN101208088A (zh) 2008-06-25
US8017635B2 (en) 2011-09-13
EP1890694A1 (fr) 2008-02-27
JP2008545744A (ja) 2008-12-18
EP1890694A4 (fr) 2010-10-27
US20100152045A1 (en) 2010-06-17
KR20080015868A (ko) 2008-02-20
BRPI0613535A2 (pt) 2011-01-18
ZA200710250B (en) 2009-03-25

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